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钯催化功能化分子中伯 C-H 键的直接硼化反应。

Direct borylation of primary C-H bonds in functionalized molecules by palladium catalysis.

机构信息

Beijing National Laboratory of Molecule Science (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Green Chemistry Center, Peking University, Beijing, 100871 (China).

出版信息

Angew Chem Int Ed Engl. 2014 Apr 7;53(15):3899-903. doi: 10.1002/anie.201310000. Epub 2014 Mar 5.

DOI:10.1002/anie.201310000
PMID:24596275
Abstract

Organoborane compounds are among the most commonly employed intermediates in organic synthesis and serve as crucial precursors to alcohols, amines, and various functionalized molecules. A simple palladium-based system catalyzes the conversion of primary C(sp(3) )H bonds in functionalized complex organic molecules into alkyl boronate esters. Amino acids, amino alcohols, alkyl amines, and a series of bioactive molecules can be functionalized with the use of readily available and removable directing groups in the presence of commercially available additives, simple ligands, and oxygen (O2 ) as the terminal oxidant. This approach represents an economic and environmentally friendly method that could find broad applications.

摘要

有机硼化合物是有机合成中最常用的中间体之一,它们是醇、胺和各种功能化分子的关键前体。一个简单的钯基体系可以催化功能化复杂有机分子中伯 C(sp(3) )H 键转化为烷基硼酸酯。在商业上可获得的添加剂、简单配体和氧气(O2 )作为末端氧化剂的存在下,使用易于获得和可去除的导向基团,可以对氨基酸、氨基醇、烷基胺和一系列生物活性分子进行功能化。这种方法是一种经济且环保的方法,可能具有广泛的应用。

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